How did a poseur like former ESPN columnist Sarah Phillips get so far in the gambling world, a place where you might expect people to value experience, wisdom, and verifiability above all else? Well, remember where she—and presumably her partner, Nilesh Prasad—got her start: the gambling message board at Covers.com.

Sports-betting boards have a logic all their own. Phillips's ascent was unusual in that it ended up with a commentary gig for ESPN. But she's far from the first person who has found a way to monetize or build a brand out of something that began as a forum handle on a sports-betting site.

Although Phillips's scammy adventure had some unexpected twists, she started just like any other person hoping to make sports betting more than just a casual endeavor—by trying to gather a following on a highly trafficked forum.

Sarah Phillips, the former ESPN.com contributor and self-professed gambling guru, is having a bit…
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The usual goal is to become a tout, or pick seller. Phillips achieved enough velocity to sail over that goal into mainstream commentary, but the elements of success are the same. What sports-gambling touts don't want anyone to know is that the job isn't really about making winning selections or possessing a strong knowledge of sports.

The picks don't matter. It's all about how you package them. Phillips and Prasad had a built-in advantage: Phillips is a young woman, and at least 75 percent of sports bettors who frequent message boards are males in their 20s, 30s, and 40s. She naturally stood out.

Most wannabe touts are forced to try to differentiate themselves in some other way. An extended hot streak will always get attention. The masses flood the boards looking for winning picks because they're too lazy to handicap games themselves (either that or they're long-term losers). The picks start out free, but as the following builds—and as the demand increases—the pick provider begins plotting the next move, trying to figure how to turn a hobby into a career.

"I have witnessed about a dozen popular handicappers on Covers go the [pick-selling] route over the years," said Big East Expert, a well-respected forum poster since 2006. "Not all bad guys, but the temptation I suppose is just too great not to cash in.

"Or at least try."

Social media and self-publishing tools have become an equalizer for amateur sports bettors looking to break into the industry as professional pick sellers. But the message boards—now and likely forever—remain the proving grounds, the minor leagues for the wannabe tout.

If a pick-selling site comes calling for a poster after a sustained win streak, going pro is a no-brainer. But those calls are few and far between, meaning the most likely path is to start a blog and sell picks independently. The pick-selling industry is poorly monitored and unregulated—a free-for-all in which every man for himself quickly becomes every scam for itself.

Some forum posters have broken into the industry and have achieved moderate success while carrying themselves with professionalism and integrity. Dave Essler, of the pick-selling site Pregame, immediately comes to mind.

But others are far more interested in parlaying short-term success into long-term financial gain, and like Phillips, they don't care whom they hurt by portraying themselves as something they're not.

Their success gives message-board posters hope. They've seen others before them make the leap and are confident they can do the same. Unfortunately, they tend to gravitate toward the boiler-room tactics popularized in the 1980s, when pick-sellers would overpromise ("guaranteed selections!") and underdeliver ("We'll do better next time!").

Online anonymity enables pick sellers to become something they aren't: Las Vegas wiseguys, Ivy League students with proven systems, and so on. It also allows them to change names on the fly, something that handicapper Brandon Lang—whose fabricated career inspired the movie Two For The Money—has done on more than one occasion (he was previously known as Brandon Scott, Brandon Link, and Mike Anthony.)

Covers recently hired a 21-year-old handicapper much the way ESPN hired Phillips: sight unseen, and without verifying the legitimacy of his background or credentials. The kid—who lied on his résumé and was fired after five days on the job—was initially perceived by Covers to be someone they could market to their audience.

"We can also brand you [as] the Whiz Kid-or the computer kid—as this is part of your daily systems for picking winners," a Covers rep told the 21-year-old in an email we obtained at Beyond the Bets. The kid, of course, had made no previous mention of using computers to pick games. (He went 3-9 in his brief career).

(Full disclosure: I used to write a column for Covers, and I worked as a freelancer for SportsDirect, the parent company of Covers, until April, when I was let go for pursuing the story about the 21-year-old handicapper.)

At Pregame, 23 of 33 handicappers (69 percent) recently lost money for clients in a documented period of time that consisted of 25,956 picks. A $100 bettor would have lost $127,708 by tailing every pick made by the "professionals"—and that doesn't even factor in the cost of the various packages, which can carry monthly fees as high as $349.

Everyday Joes who regularly post their plays on sports betting forums are convinced they can do better and want the opportunity to prove it—if not at a major company's website, then perhaps on their own.

Wannabe touts who aren't successful will sometimes try to steal the identities of those who are. The aforementioned Big East Expert has no intention of ever selling picks (he works at a Fortune 500 company) but recently found himself in the middle of a scam anyway.

An impostor copied his forum handle and avatar, created a Twitter account, and then began selling picks on the Internet—hoping to trick unsuspecting suckers who didn't know any better. It's apparently working. The impostor's website carries a respectable Alexa traffic rank (188,664 in the U.S.) and is selling yearly picks packages for $845.

This is the world that helped create Sarah Phillips—a world where everything is a commodity, not least your own identity. It was natural for the audience on the boards to wonder if she was real. They have to wonder that all the time.